Diphenyl-dimethyl-aminovaleramide



Patented Aug. 4, 1953 DIPHENYL-DIMETHYL-AMINOVALERAMIDE Merrill Eugene Specter, Kalamazoo, Mich., as-

.signor to Bristol Laboratories Inc., Syracuse,

N. Y., a corporation of New York No Drawing. Application June 12, 1952, Serial No. 293,195

Claims. 1 This application :is a continuation-impart (of my co-pending application of :Serial Number 2 AnaZysis.Calculated for C19'H24N2OZ 12.6015, filed-November 7, 1949,.andrSerial'Numoamlated Found ber 187,656, filed September 29, 1950, both .now abandoned. 5 76.96 76.90 76.90 This invention relates :to .a new organic -.com pound of therapeutic value and a method for the preparation thereof. More particularly, this invention relates to a,a-diphenyl-v-dimethyl- METHOD B aminovaleramide and non-toxic organic and in- Forty-five 1, of concentrated sulfuric id anic acid addition salts thereof. (98%) was diluted with 5 ml. of water to give a 0 solution of approximately 92% sulfuric acid. To CHHS QL this was added five grams (0.018 mole) of diphenyl 'y dimethylaminovaleronitrile. The mixture was heated on a steam bath two hours 05H. OHzOH-N and was then cooled. The mixture was poured l CH3 onto ice and neutralized with concentrated ammonium hydroxide. The White solid was filtered The compounds of the P11859111? mVenFmn and recrystallized from isopropyl alcohol. The sess therapeutic utility by virtue of their lack of material melts at 0 and this value was toxicity and their ability to suppress gastric senot changed when a sample was mixed with the cretion of acid and to dilate the pupil of the eye. product from method (A) These activities have been reported in detail by Wellum and Pollard (J. Lab. and Clin. Med, E AMPLEII August 1951) and by Drucher and Cazort (Ar- Alpha, l h di h n l gamma dimethylaminochives of Ophthalmology, June 1951) respectively. The following examples will serve to illustrate the invention without limiting it thereto.

EXAMPLE I oaleram de acid sulfate hydrate 252.0 grams (0.85 mole) of alpha, alpha-diphenyl gamma dimethylaminovaleramide was dissolved in 1 liter of isopropanol, and 70* ml. of concentrated sulfuric acid was added as rapidly p enyl-v-d1.methylammovaleramzde as possible. The mixture was heated until clear,

. then filtered and diluted with 1500 m1. of anhy- 0611, GN 0,115 L drous ethyl acetate. The solution was cooled and filtered, and the white crystalline product was C dried in vacuo over P205. 011. om-on n C5115 oHr-oHN( a) Weight: 259.5 g.; M. P. 181.5182 C. (gas ('33, 0113 H3 GVOIUtiOI'l) METHOD A EXAMPLE III A mixture of 14 grams (0.05 mole) of a,a-di- 40 Alpha g gfig i gggfig fgggz phenyl-ydimethylaminovaleronitrile, 16 grams (0.2 mole) of sodium acetate, 14 grams (0.2 mole) A solution of 11.0 g. (0.037 mole) of alpha, alof hydroxylamine hydrochloride and '75 ml. of D a p y gamma d y a e ethyl alcohol was refluxed 18 hours. The mixamide in 250 ml. of dry chloroform was saturated ture was cooled, poured into water and neutralwith dry hydrogen chloride, and the chloroform ized with ammonium hydroxide. The heavy was removed by distillation. The residual glassy white precipitate solidified on standing. The masolid was recrystallized from. absolute ethanolterial was filtered and recrystallized from isoether and dried in vacuo over P205. It was quite propanol. After three recrystallizations the hygroscopic. Yield: 10.2 g.; M. P. 190.5-l91.5 product melted at 177-179 C. C. (gas evolution).

The invention also includes the non-toxic, organic and inorganic acid addition salts of the compound having the general formula above such as will be readily formed with, for example, organic and inorganic acids such as hydrochloric, sulfuric, sulfamic, tartaric, hydrobromic, hydriodic, glycolic, citric, maleic, phosphoric, succinic, acetic, benzoic, cinnamic, mandelic, malic, ascorbic, and the like. The method of preparation of these salts is made apparent in the examples above.

I claim:

1. A new class of compounds consisting of the free base and the non-toxic acid addition salts thereof, said free base having the formula CaIs CHr-(IJHN CH3 CH3 2. The non-toxic acid addition salts of a,a-

diphenyl-'y-dimethylaminovaleramide.

3. The compound 4 CH: ("I-NH:

on. Cl; om-oH-N 6H: CH3

a,a-diphenyl-'y-dimethylaminovaleramide.

4. The compound a,a-dipheny1- -dimethylaminovaleramide acid sulfate hydrate.

5. The compound a,a-diphenyl-y-dimethylaminovaleramide hydrochloride.

MERRILL EUGENE SPEETER.

References Cited in the file of this patent FOREIGN PATENTS Country Date France Feb. 22, 1943 OTHER REFERENCES Number 

1. A NEW CLASS OF COMPOUNDS CONSISTING OF THE FREE BASE AND THE NON-TOXIC ACID ADDITION SALTS THEREOF, SAID FREE BASE HAVING THE FORMULA 